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. Author manuscript; available in PMC: 2022 Nov 19.
Published in final edited form as: ACS Chem Biol. 2021 Sep 27;16(11):2502–2514. doi: 10.1021/acschembio.1c00597

Scheme 1. Synthesis of Disaccharide Oxazoline 7 Carrying Two Azide Tagsa.

Scheme 1.

aReagents and conditions: (a)DDQ, CH2Cl2/H2O, 0 °C ~ RT, and 90%; (b) BH3·THF, Bu2BOTf, CH2Cl2, 0 °C, and 94%; (c) AcSH, pyridine/CHCl3, RT, and 82%; (d) N3(CH2CH2O)3Ts, NaH, DMF, 0 °C ~ RT, and 78%; (e) NaBrO3, NaS2O4, EtOAc/H2O, RT, and 65%; and (f) DMC, Et3N, H2O, 0 °C, and 90%.